Downtown Chicago

The annual City of Chicago tree lighting ceremony takes place in late November in a festive event which includes live entertainment. 2024 marks the 111th anniversary of the city’s kickoff to Christmas. The first official tree was lit in Grant Park back in 1913. On an interesting historical note, the first tree was only 35 feet tall. The tallest tree was an 85 footer in 2008! Note: The tree used to be located in Daley Plaza (staring in 1967) for many years, but moved to Millenium Park in 2015 where it still stands today.

The Chicago Christmas tree at Millennium Park

What to do nearby: Ice skate at Millennium Park, one of the most beautiful urban rinks in the country and it’s free! As a Chicago native, I also highly recommend Lincoln Park Zoo Lights and the annual screening of “It’s a Wonderful Life” (we got to meet Karolyn Grimes who plays ZuZu one year!) at Hollywood Blvd.

Also, the Great Tree at the Walnut Room at Macy’s on State Street is amazing. You will need reservations (which are quite hard to get) to dine alongside this beautiful 45 foot tall hanging tree. The theme for 2025 was so old-school and nostalgic: a gorgeous Marshall Fields theme as a nod to the store’s beginnings in 1914.

The Great Tree at The Walnut Room on Macy's on State Street in Chicago

Village of Tlaquepaque: Sedona, Arizona

Beautiful Sedona Arizona is home to marvelous 250 million year old red rock formations. While there is plenty of fabulous red rock hiking to enjoy year-round, during the month of December you can also enjoy some seasonal events. I find the events here much different than most of the country, so I give them bonus points for the creativity.

The gorgeous tree at the Village of Tlaquepaque provides a wonderful festive backdrop for local dining and shopping. Visits with Santa and live entertainment accompany this free event. Also look into the annual lighting of the luminaries event held mid December. During this 48+ year old tradition, more than 6000 luminaries are lit.

Update: The luminaries event has been cancelled. however, the plaza still looks beautiful and there are a lot of great local businesses to support. I love dining at El Rincon – the serve great burritos and Navajo pizza!

Christmas tree at the Village of Tlaquepaque in Sedona

Uptown Sedona

Sedona, Arizona is easily one of the most gorgeous vacation destinations in the US. If you love hiking, the outdoors, and healthy food, you will love it here. Winter is actually a great time to visit as the tourist crowds have finally disappeared, leaving you alone with awe-inspiring red rock views. I was a local of Flagstaff for many years and winter was my favorite time to hit the trails and explore Uptown in peace.

If you are lucky enough, you may just get to see the red rocks dusted with rare snow. Uptown is home to all sorts of great local boutique shops and restaurants. I picked up so many cute cacti and Southwest themed gifts and souvenirs here.

The tree is beautiful as are all the lovely decorations. The annual tree lighting includes live music and festive treats. This is one of the more unique trees I’ve come across – where else can you see a tree surrounded by 200+ million year old ancient rocks?

Christmas tree in Uptown Sedona surrounded by red rocks

What to do nearby: Stroll around and enjoy the unique boutique shops and restaurants of Uptown. Black Cow is a great little ice cream shop (I recommend the prickly pear). I also recommend Wildflower Bread (their soups and salads are so good), Salt Rock Southwest Kitchen, and Elote Cafe.

Boston Common: Boston, Massachusetts

Every year, the first week of December, the City of Boston (plus guests from Nova Scotia) light the annual Christmas tree. Accompanying the lighting are stage performances plus the unveiling of the lights at Boston Common and Public Garden.

2024 marked the 83rd anniversary of the tradition with appearances by Santa Claus and Rudolph, performances by Darlene Love, and a special appearance by the cast of A Christmas Story: The Musical. On an interesting side note, every year the people of Nova Scotia give the city a tree as a thank you for their assistance following the Halifax Explosion of 1917.

While living in Fall River (a quick drive to the city) for many years, I enjoyed many holiday daytrips, mainly to ice skate. I loved that I could grab a coffee or cocoa and stroll around this lovely tree after enjoying my favorite holiday activity.

Christmas tree in downtown Boston

What to do nearby: Go ice skating at beautiful Frog Pond – it’s a beautiful city rink and they even host a few professional skating performances here each year. Also, this is a great time of the year to walk The Freedom Trail. Yes, it will be cold, but it will also be much less crowded. I love photographing the architectural masterpieces and exploring at my own pace without a bunch of tourists around.

Heritage Square: Downtown Flagstaff, Arizona

Christmas tree at Heritage Square in Flagstaff, Arizona

Flagstaff is a gorgeous mountain town in Northern Arizona that I had the opportunity to live in for a few years. With over 200 inches of snow per year, this high altitude winter wonderland is a popular escape for Southern Arizona residents seeking a traditional wintry ambiance. The small town offers a lot in terms of winter activities including a ski resort, miles of snowshoeing trails, and snow tubing. I’ve see hundreds and hundreds of cars lined up to get to the ski resort almost every winter weekend.

There is a small, but lovely tree in Heritage Square. A fresh dusting of snow adds to the ambiance. While small, the tree is lovely especially with the small town mountain charm. The red bows really stand out and for some reason, this tree just looks so enchanting to me when dusted with snow.

What to do nearby: The downtown is loaded with great local restaurants. I recommend Beaver St. Brewery for delicious pub food and Mix for their delicious salads. As for winter activities, there’s lots to do including nordic skiing, cross country skiing, snowshoeing, and more. My winter guide will give you the full details.